This subproject is one of many research subprojects utilizing the resources provided by a Center grant funded by NIH/NCRR. The subproject and investigator (PI) may have received primary funding from another NIH source, and thus could be represented in other CRISP entries. The institution listed is for the Center, which is not necessarily the institution for the investigator. This work would involve the production of novel biologically active molecules, in particular we would center on compounds designed to have anti-microbial and anti-fungal properties. This organic synthetic research would center on the production of heterocycles from 1,3 [unreadable]dipolar cycloadditions with nitrile oxides or nitrosilonates as intermediates. The proposed anti-microbial project would involve the challenge of attaching these smaller units together to form a macrocycle that could function as an ionophore. The anti-fungal project would involve an investigation into the synthesis of a novel class of compounds. It is expected that it will be very easy to change a number of variables in these potential polyester macromolecules and isoxazole fungicides. For example the symmetry of the macrocycle could be examined by altering the symmetry of the 3,4-substituents of the tetrahydrofuran ring. The functionality of the macrocyclization could be changed from polyester to polyether to polyamide. Thus there are many variables that could be exploited to produce a series of macrocycles with excellent bindings of metal cations. This research project would be an excellent opportunity for many students interested in both the chemistry and biology behind biomedical research.